Best Dress Shoes for Toddlers with High Insteps – Stylish, Affordable, and Extra Deep!

April 23, 2025 High Instep Juan Valenzuela 0 - Comments

Struggling to find toddler dress shoes that fit a high instep? Many parents try multiple pairs, only to end up frustrated. The instep—the raised top part of the foot—can make it tough to find a comfortable fit in standard dress shoes. As an experienced shoe fitter, I’ve helped many families in the same situation. In this guide, I’ll show you the best dress shoes for toddlers with high insteps that provide both comfort and style.

How Does a Foot with a High Instep Look Like?

A high instep means the top of the foot is fuller or puffier. Take a look at where the instep is located—it’s the raised area on top of the foot. When toddlers have high insteps, there’s extra volume that needs to be comfortably accommodated inside the shoes, which is why finding the right fit is so important.

^{An image of a toddler with a high instep.}

I’ve heard from countless parents of toddlers with high insteps who’ve spent hours visiting stores and ordering shoe after shoe online—only to end up frustrated with poor fit or quality. The truth is, only a few dress shoes are designed to accommodate a high instep. The good news? I’ve personally fitted these styles and know exactly which ones work best for comfort, support, and fit.

Be Careful About Buying the Wrong Types of Dress Shoes

I’ve noticed that some parents don’t think too much about which dress shoes to buy for their toddlers—after all, they’re usually worn just occasionally and for short periods. But here’s the thing: it only takes a few wears in the wrong size or style to cause blisters, calluses, or even long-term foot issues. Choosing the right dress shoes matters more than you might think—your toddler’s comfort and foot health depend on it.

Key Features of Dress Shoes for Kids with High Insteps

When selecting dress shoes for toddlers with high insteps, consider these features:

1. Extra Depth: Shoes with extra depth provide more space for the foot, ensuring a comfortable fit without squeezing. This feature is vital to accommodate the additional height of the instep, allowing for natural movement and avoiding pressure on sensitive areas.

^{Notice how the shoe on the right offers significantly more depth than the one on the left? You can see the difference in height across both the instep and toe box—providing extra room for a more comfortable fit.}

^{Now let’s take a look at two different Mary Jane styles for toddler girls. See how the one on the right offers much more depth than the one on the left?}

2. Adjustable Closures: Look for shoes with velcro straps or laces that allow you to adjust the fit according to the foot’s height. Adjustable closures offer flexibility in fit and can accommodate minor changes in foot size, making them ideal for growing toddlers.

^{A sleek pair of toddler black dress shoes featuring double Velcro straps—perfect for easy on and off, all while offering a secure and stylish fit for special occasions.}

All of the dress shoes I recommend below provide these two important features to accommodate your toddler’s high instep. Disclosure: This post contains affiliate links. We may earn a small commission—at no extra cost to you—if you make a purchase.

Best Dress Shoes for Toddlers with High Insteps – Extra Deep

Here’s my curated list of the best dress shoes for toddlers with high insteps in 2025. Along with extra depth, several of the dress shoes below also come in wide (W) and extra wide (XW) widths—giving your toddler the comfort and space they need for a perfect fit.

1. Willy by FootMates

These white versatile dress shoes for high instep feature a flexible outsole that promotes natural foot movement and a breathable lining to keep little feet comfortable.

Order the shoe Willy by FootMates on Zappos or Amazon
Available in medium and wide widths
Removable, dual insoles in medium and wide are provided to allow customized fitting
Breathable leather lining and cushioned leather-lined footbed cradles children’s feet
Ideal for formal occasions and casual wear
Lace-up design
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

2. Allie by Footmates

These deep Mary Jane shoes for toddlers with high insteps feature a leather upper that provides a classic look, while the cushioned footbed ensures all-day comfort.

Order the shoe Allie Mary Jane by Footmates on Amazon or Zappos
Fits toddlers with medium or wide feet
Easy on-and-off with an oversized opening hook and loop closure
Rounded, slip-resistant soles encourage natural motion and help improve balance
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

3. Brian by Deer Stags

This deep dress shoe offers a timeless aesthetic that pairs well with any formal outfit. The shoe’s design is versatile enough to transition from casual to formal settings, making it a smart investment for parents.

Order the shoe Brian by Deer Stags on Zappos or Amazon
Available in medium and wide widths
Padded insole
Dual goring at vamp
Ideal for formal occasions and casual wear
Slip-on design
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

4. Shoe style Holly Mary Jane by Stride Rite

This wide Mary Jane is both stylish and practical, perfect for dressier occasions. It provides extra depth and comes in extra wide widths to accommodate the shape of toddlers with high insteps and very wide feet.

Key Features

Order the shoe Holly by Stride Rite on Zappos or Amazon
Available in extra wide widths
Awarded the Seal of Acceptance from the American Podiatric Medical Association (APMA)
Padded tongue and collar for added comfort
Supreme comfort care of Ortholite memory foam footbeds
I suggest that you get this Mary Jane shoe a whole size larger than your toddler’s current foot size

5. Gamefish by Sperry

These dress shoes for toddlers with high insteps offer a unique blend of style and functionality. The round toe-box ensures a comfortable fit, even for those with wider feet. This shoe appears to have laces but it comes with a hook-and-loop closure for easy on and off.

Order the shoe Gamefish Jr. by Sperry on Zappos or Amazon
Available in medium and wide widths
100% genuine leather upper
Velcro closure
Alternative closure with fixed lace for easy on/off and adjustability
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

6. Holly by Stride Rite

These deep Mary Janes feature cushioned insoles and flexible outsoles, providing the support and comfort toddlers need. The classic design makes them suitable for various occasions.

Order the shoe Holly by Stride Rite on Zappos or Amazon
Fits toddlers with medium or wide feet
Leather lining for a soft feel
Lightly padded leather insoles
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

7. Loafer by French Toast

These high instep dress shoes for toddlers offer a blend of style and practicality.

Order the shoe Loafer Church by French Toast on Amazon
Also available with laces
Fits toddlers with medium or wide feet
Padded tongue and collar provide additional comfort and cushioning
Genuine leather
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

8. Bianca Mini by See Kai Run

See Kai Run’s Bianca black Mary Jane shoes are designed with comfort in mind. The breathable materials and padded collar ensure a comfortable fit, while the round toe-box accommodates little toes.

Order the shoe Bianca Mini by See Kai Run on Amazon or Zappos
Fits toddlers with medium and wide feet
Cotton canvas lining and leather sockliner keeps feet dry and fresh
Generous toe box provides room for healthy foot development
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

9. Lonsoen Lowfur

The Lonsoen loafer combines fashion with function. These shoes feature a soft, flexible sole that supports natural movement, and the extra depth makes them a great option for toddlers with high insteps.

Order the shoe style Soft Slip by Lonsoen on Amazon
Fits toddlers with medium or wide feet
Padded tongue and collar provide additional comfort and cushioning
100% synthetic
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

10. Allie Mary Jane by Footmates

These wide width Mary Jane shoes for toddlers provide extra depth for easy on and off, which makes it ideal for toddlers with wide feet and high insteps.

Order the shoe style Allie Mary Jane by Footmates on Amazon or Zappos
Fits toddlers with medium or wide feet
Easy on-and-off with an oversized opening hook and loop closure
Buckle closure for a secure and adjustable fit
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

11. Oxford by Meckior

These wide oxford shoes for toddlers with high insteps are crafted with high-quality materials that offer both durability and style.

Order the shoe style Soft Slip by Lonsoen on Amazon
Fits toddlers with medium or wide feet
Lace-up closure
Made from soft PU leather material
I suggest that you get this dress shoe a half size larger than your toddler’s current foot size

12. Mary Jane by FunkyMonkey

These toddler Mary Jane shoes by FunkyMonkey are a classic choice for little girls. Its adjustable strap ensures a snug fit, while the cushioned footbed provides all-day comfort.

Order the shoe style by FunkyMonkey on Amazon
Fits toddlers with medium or wide feet
Velcro buckle secures the perfect fit every time
Lightly padded leather insoles
I suggest that you get this dress shoe a whole size larger than your toddler’s current foot size

How to Order the Correct Shoe Size Online

I understand the temptation to leave a little extra growing room in your toddler’s dress shoes—especially since they may not wear them often. But too much space can affect your child’s stability and comfort. There’s a safe way to give growing room without compromising fit, and I’ll explain how in just a moment.

To make things easier, I created a virtual shoe fitting service that helps you measure your child’s foot size accurately from home. This simple tool will not only determine your toddler’s exact size, but also reveal whether they have narrow, wide, or extra wide feet—and if they have a high instep that needs to be accommodated.

Contact Me for Specific Shoe Recommendations

Every child’s foot is unique, and finding the right shoes involves considering individual needs. If you need specific recommendations tailored to your toddler’s foot shape, feel free to contact me via email. I’m here to help you find the perfect pair that combines style, comfort, and functionality.

How to Tell if Your Toddler Has a High Instep?

Sign One: If your toddler struggles to put on or take off shoes, this could be a sign of a high instep. The shoes may feel too tight across the top of the foot. Such struggles can lead to frustration for both the child and the parent, highlighting the need for the right shoe fit.

^{An image of a father struggling to get her daughter’s shoes on.}

Sign Two: After wearing shoes, if you notice red marks or imprints on the top of the foot, this indicates that the shoes are too snug in that area. Over time, these marks can lead to irritation and discomfort, making it crucial to address fit issues promptly.

^{An image of a toddler with imprints on the top part of his foot from wearing narrow shoes.}

Sign Three: If the velcro straps don’t reach the end or barely close, it might be due to the shoes not having enough depth to accommodate the high instep. This can limit the shoe’s adjustability, potentially causing pinching or pressure points on the foot.

^{An image of a toddler wearing a pair of Saucony shoes that are not deep enough for his foot.}

Bonus Resource: Sneakers for Kids with High Insteps

In addition to dress shoes, finding the right pair for everyday wear is crucial for your child’s foot health. Sneakers designed for high insteps often include features like extra depth, round toe boxes, and adjustable closures. These elements provide the comfort and support necessary for daily activities.

The importance of choosing the right shoes for toddlers cannot be overstated. Proper footwear during the early years can significantly impact foot development and overall comfort. Ensuring that your child’s shoes are supportive and well-fitting is essential for their health.